John F. Kennedy Jr: America’s Reluctant Prince

Steve Gillon: When I met John F. Kennedy Jr in 1982, I stood firmly in the conspiracy camp. It was settled history, and I never raised the topic with him. It came up only once, around the time when director Oliver Stone’s conspiratorial film JFK hit theaters in 1991. Stone challenged all the major conclusions of the Warren Commission, established by Lyndon Johnson and chaired by the chief justice of the Supreme Court, Earl Warren, by charting the path of the “magic bullet” as it meandered through Kennedy’s body and then Governor Connally’s. Clearly, they claimed, there must have been at least two shooters, maybe even more. It seemed by the end of their presentation that everyone in Dealey Plaza that day, with the possible exception of Mrs. Kennedy, had a motive to kill Kennedy. The military, the Secret Service, the CIA, the FBI, and the Mob apparently conspired with various outside forces—the Soviets and the Cubans—to murder JFK and then orchestrate a cover-up. I don’t recall the context of the conversation, but John stated cryptically, “Bobby knew everything.” By December 1995, Director Oliver Stone had just released a new movie about the late Richard Nixon, who died a month before Jackie in April 1994, and it was generating a lot of buzz. It seemed like an ideal fit for John's magazine George to produce a cover depicting a blockbuster Hollywood movie about a controversial American president. But it turned out to be a poor decision. A clueless Eric Etheridge suggested that John meet with Stone to discuss the content of JFK. John was shocked. Anyone who knew him understood that his father’s death was off-limits. John replied bluntly, “It’s not entertainment for me.” I spent many hours talking with John about his father and his presidency, but we rarely broached how he died. He made only two cryptic comments. On the thirtieth anniversary, in November 1993, considerable news coverage rehashed the assassination. And he said enigmatically, “Bobby knew everything about my father’s killers,” and he said it in a way that made me think perhaps Bobby knew things that the public, and maybe even the Warren Commission, did not know.

John Kennedy Jr had heard rumors that Carolyn Bessette liked to party, so he asked a friend who had connections in the Manhattan nightclub scene to investigate and report back to him. The friend, who wishes to remain anonymous, recalled that he did not deliver a “flattering” report. “She does a lot of blow, she stays out late, she knows how to play guys. Be careful.” John not only ignored this advice, he also told Carolyn everything he’d heard. She never forgave the friend. While preparing to launch his George magazine, John arrived at another important decision: to marry Carolyn. Their relationship had deepened in the year since Jackie’s death, and John had grown convinced that Carolyn was the one for him. He had fallen in love with her and considered her the first girlfriend who could see beyond the veneer of his fame and celebrity. Carolyn teased him and stood up to him because of her independent, passionate personality—qualities that John found attractive. Naturally, their relationship veered between extremes of emotion. Sometimes, they could not seem to take their hands off each other, while at other times, they fought with equal intensity. “They were fiery,” recalled Ariel Paredes, a mutual friend. “They would love hard and they would fight hard but they were very much a couple in love.” In November 1994, John officially introduced Carolyn to his only remaining immediate family members—his sister, Caroline, and her husband, Edwin Arthur Schlossberg. Carolyn moved into the 2,000-square-foot penthouse in Tribeca that John had purchased shortly after his mother died. 

After their wedding on September 21, 1996, which was kept secret from the press, on the remote Georgia island of Cumberland, Carolyn started to suggest changes in the George magazine staff, and John's partner Michael Berman didnt like her suggestions. He ripped into Carolyn, telling John, “Get her the hell out of the office.” John, caught off guard by Michael’s seemingly unrelated attack on his wife, rushed to her defense. “You have no idea!” John shouted back. “Don’t say that about her. She has legitimate friends in this office.” He told Berman that he was jealous because they liked her but did not like him. “She’s the best thing that ever happened to me. Why would you try to ruin that? I can’t tell her what to do.” Berman snapped. “Her behavior is deplorable!” he shouted. As if to mark the end of their partnership, John bought out Michael’s 25 percent share, thus assuming half ownership of the magazine. Michael Berman never spoke with John again.

For the most part, John liked to play sports and engage in physical activities with his male friends. But he’d confide in his female friends, and none more so than old pal Sasha Chermayeff. By the late 1990s, she had married and was raising a kid. John called her the morning after she gave birth to her first son. “Sasha, did you have your baby?” he asked. John was ecstatic when Sasha said yes and told him her son’s name: Phineas Alexander Howie. John was Phineas's godfather. Sasha said about the rumors of turmoil in John & Carolyn's marriage: "It’s impossible to know the intimate details of John’s and Carolyn’s private lives, but from all the available evidence, it appears highly unlikely that John was having an affair." In fact, he had confessed to several friends, “I wish I could cheat on her but I can't.” Carolyn was not opposed to having children but found John’s timing mind-boggling. “We are in the middle of complete chaos here,” she told him. “You are flying around trying to find funding for your magazine, we are dealing with your cousin Anthony dying, and you want to start a family.” Still, John could not understand her reluctance. “What does she want? Like her life is so hard.” John once complained to RoseMarie Terenzio. Carole Radziwill, however, saw no evidence that John and Carolyn’s marriage was careening toward a divorce. “There was nothing, not one conversation, nothing to indicate that there was an impending divorce,” she recalled. 

“It’s certainly easy to sit around and talk about arguments and fights, but very few people knew what was going on.” The last six months of their lives were stressful: they were fighting over many different issues, and the shadow of Anthony Radziwill’s death hung over them. Carole Radziwill used the metaphor of a husband and wife having an argument in a fast-moving car when they crash into a wall and are killed. No one knows how that conversation would have ended. The same was true of John and Carolyn, she maintained. “He loved her, and she loved him,” she reflected. “But they also drove each other crazy.” John confided to Robert Littell that he worried the magazine would likely come to an end. His efforts to keep George afloat had clearly taken a toll on him. According to Littell, “he'd gained weight, he looked tired, his hair was noticeably grayer.” Steve Gillon was and old acquaintance of John and visited John & Carolyn's Tribeca apartment. Gillon recalls: We walked down a busy street, populated with countless bars and restaurants, onto a dark side street with only one dimly lit streetlamp. “Why would John live here?” I thought, as I scanned a neighborhood full of abandoned warehouses. His building looked like an outdated industrial factory. We entered a small, nondescript lobby with linoleum floors. No doorman. No security. He used another key to call the elevator. John’s apartment was on the top floor of a nine-story building. The apartment was dark, so I did not get to see much other than some mismatched furniture. Somehow I’d imagined John living in a fancy high-rise with a doorman and dramatic floor-to-ceiling windows. But John was always the rustic type. He would have been perfectly comfortable living in a tent in Central Park. As we walked in, John told Carolyn that he had brought a friend over to read “the Hachette letter.” I told him that this letter would almost definitely serve as Hachette’s defense for refusing to renew the contract with George magazine. It represented a clear warning shot, putting John on notice that if he protested, they would go after him personally.

At this point, Carolyn jumped into the discussion, enraged. I knew that she was fiercely protective of John, but I never expected what followed: a string of expletives like I had never heard before. “John, they are trying to fuck you!” she shouted loudly. “Everybody fucks you, John, and you just take it! You let everybody fuck you, John. When are you going to grow some balls and start fighting back? You need to start fucking people back, John.” John solemnly guided me out of their apartment. He said he needed to clear his head. When we got to the curb, I shook his hand and turned right toward the civilization. John turned left down the dark street. After taking a few steps, I turned around and saw his silhouette, head down and hands in his pockets. It was the last time I would ever see him. John’s relationship with his sister hit rock bottom in the summer of 1999. The visits to see her and her children—Rose, Tatiana, and Jack—whom he adored, had become less frequent. It was not the relationship that either wanted, but John could not stomach being in the same room with his brother in law. 

Despite being under enormous pressure, John was still capable of gestures of empathy and generosity. I learned that firsthand. In the spring of 1999, I had developed a tremor in my left arm, along with unexplained twitches throughout my body. By this point, I had left Oxford and accepted a position as the dean of the Honors College at the University of Oklahoma. Theoretically, the move made it easier for me to commute to New York to tape my History Channel show, but since there were no direct flights, it actually took longer. John noticed something was wrong one day while we played racquetball. During our last game, roughly a week before his Buckeye accident, I held out my left hand and showed him the tremor. I put on a brave face, telling him I was too afraid to visit a doctor. Without prompting, John started talking about Anthony and how courageous he was in dealing with his horrible disease. John never told me that Anthony was dying. All he talked about was how Anthony refused to complain. He used the word 'tough' a handful of times, as if prodding me to follow Anthony’s example. On Friday, July 9, I finally decided to make an appointment to see the chief of neurology at the University of Oklahoma Medical Center. I had convinced myself that I suffered from Parkinson’s disease, but I decided to see a doctor who could confirm my self-diagnosis. At the end of the tests I sat on the table and asked the neurologist, “So do I have Parkinson’s?” He shook his head and said, “Well, I have good news and bad news.” The good news was that I did not have Parkinson’s; the bad news was that I could be in the early stages of ALS, popularly known as Lou Gehrig’s disease.

After listening to my detailed description, John started speaking. I can still hear his voice. “For better or worse,” he said, “my family is well connected in New York medical circles. If there’s anything you need, you let me know.” There was then a pause. “Stevie,” he said, “I’ll take care of you.” To make sure that I heard it right the first time, he repeated. “I’ll take care of you, Stevie.” He then added: “And don’t worry about all that insurance stuff.” Only later did I discover that he suffered from Graves’ disease, a thyroid disorder that required him to drink a disgusting concoction of iodine and seltzer. Apparently, anxiety only aggravated the problem. He was having trouble sleeping, often waking up at five o’clock, leaving him completely drained at work. John initially thought that Jann Wenner, the founder of Rolling Stone magazine, would at least offer constructive comments. “Politics doesn’t sell, it's not commercial,” Jann told him bluntly, suggesting that only 15 percent of any generation find government or public affairs interesting, but John dismissed the observation. He then proceeded to offer John a job at Rolling Stone. John suspected that Wenner simply did not want the competition. “John was hurt and felt betrayed by Jann,” a colleague recalled. Cousin Bobby Kennedy Jr., Robert and Ethel’s third oldest, praised John's ethics: “John has a tremendous sense of duty and responsibility. Whenever any of the cousins need help on one of their charity projects, John always participates.”

John F. Kennedy’s only son would grow into a remarkably well-adjusted adult, which no doubt owes a great deal to his attending psychological therapy continuously his entire life to alleviate his proclivity to depression. One question has crossed my mind more than a few times: How much of John’s personality was shaped by the trauma of his father’s death? For answers to that question, I turned to Dr. Susan Coates, clinical professor of medical psychiatry at Columbia University and a leading expert in childhood trauma. Coates pointed out that a large body of literature has identified general characteristics exhibited by children who experience trauma. She explained that three-year-olds do not understand the finality of death, but they “take their cues in understanding a traumatic loss from their primary attachment figure, who is most often their mother. In John’s case, he would have known that something very terrible had happened from observing his mother’s reaction.” For John, his father’s violent death marked the first in a series of traumatic events that would shape his personality. “In one fell swoop, he loses his father. He loses his mother in the sense that he has lost her emotional accessibility because she is in mourning. He also loses his home, the White House. It is an overwhelming trauma for the child.” Psychiatrists refer to this repetition as “strain trauma.” As Coates explained, “Although single traumatic events can have a big impact on a person, what most often shapes character are interpersonal experiences, that happen over and over again.” 

Robert T. Littell: John F. Kennedy Jr. met Carolyn Bessette in late 1994. Their attraction was instant and mutual. They began to date, secretly at first, I think because they both enjoyed the mystery. Carolyn was a blue-eyed public-school graduate from Greenwich, Connecticut, and was working for Calvin Klein at the time as a personal shopper. John first saw her while shopping for suits. He asked someone who she was, he got her phone number, and they went out on a first date in Tribeca. In one of his breaks during his long relationship with Daryl Hannah, John had enjoyed a fling with Madonna. Not a real fling, actually, more of a curiosity encounter. Madonna also alluded that sex with John had been “vanilla” for her standards and he called him “an innocent in bed.” John had dated over 50 women but he now knew he’d hooked with the one right away. By then I’d known John for twenty years. To his credit, John had a healthy libido but almost always resisted the sexual opportunities that came his way, preferring real relationships. And with people who completely lost their balance around him, he knew how to be polite but distant. It’s no coincidence that I met my future wife, Frannie, and my best friend, John, in my first week at Brown University. I met Carolyn Bessette for the first time at John’s apartment when they had just begun to get serious. He kept telling me that I should stay another minute because he had a surprise. The minute turned into an hour, but finally the buzzer rang. John became uncharacteristically jumpy. Bam! In walked the hottest girl I’d ever seen in my life. Tall, blonde, svelte, in loose-fitting jeans and a big blue shirt, she literally glowed.

Carolyn said hello to me and turned to John. From somewhere, he pulled out a cigarette—a sure sign he was a wreck because he rarely smoked. She was both shy and fierce, skilled in the acid-tongued banter that vulnerable people use to cover their soft spots. When Carolyn let down her guard, which wasn’t often, you could sense something wounded about her. I always chalked it up to the father who was so conspicuously absent from her life. Her vulnerability, while hidden beneath a tough, funny exterior, made her deeply empathetic to others. You had to meet Carolyn only for an instant to understand why she captivated John: She was almost preternaturally intense, with an electricity about her that nearly, though not quite, distracted you from her physical beauty. The qualities that John always liked in women—mystery, drama, irreverence and beauty—Carolyn had all in abundance. According to John, Carolyn resisted his proposal for an entire year. Playing hard to get? Maybe. I can’t imagine that too many women would have refused John's proposal, knowing he was madly in love. Which he was. Over July 4 in 1995, John and Carolyn went to Martha’s Vineyard to go fishing. “I wanted to go fishing like I wanted to cut off my right arm,” Carolyn confessed. John took her out on the boat, knelt down on one knee, and said, “Fishing is so much better with a partner,” as he pulled out a platinum band sparkling with diamonds and sapphires—a replica of his mother Jackie's wedding ring. Back at the Downtown Athletic Club, over an onion soup, John continued to assert that he didn’t have a doubt in his mind that he’d found the right woman. I know they were physically compatible because when I made the standard locker-room query about sex, John whispered blissfully, “Oh, my God,” and closed his eyes.

I gave him one piece of advice, which is that marriage is a decision. I said that once you make the decision to get married, you can’t spend your time longing for the greener grass over the fence. John replied, without any hesitation, “I know that.” By the time John got married, he was living in an apartment on North Moore Street in Tribeca. It was a beautiful place, though modest relative to his means. He was ready and eager to start a family when he met Carolyn. Though John might get momentarily angry when someone took advantage of him, he never held a grudge. But if Carolyn perceived that someone was using John, she went into battle mode. I’d hear about it when a banished friend would call me, trying to figure out why he’d been tossed aside from John's orbit. As 1998 progressed, John grew more frustrated with Carolyn’s troubled transition, but he also felt an enormous responsibility for her happiness. They lived out a complicated dynamic, resenting the demands each placed on the other while at the same time empathizing with the other’s frustrations. John felt hog-tied by not being able to solve Carolyn’s problems with the paparazzis. We talked a lot about this during the second year of their marriage. He hated the illogic of the whole thing: in his mind, they had so much.

There were so many reasons to be happy. But he also knew that Carolyn’s coping mechanisms had been overwhelmed. I listened and felt bad for both of them, but I told him it would get better. My wife Frannie had suffered a bout of depression in the early nineties, after quitting smoking, and she’d barely left the apartment for a year. I was confident that they’d come out the other side of this dark cloud, and John believed so, too, despite his frustration. John suffered from Graves’ disease, a thyroid disorder, for which he took iodine supplements and ginseng. He had constant emotional highs and lows, someone might even call it a bipolar disorder. After the plane crash, for reasons I don’t fully understand, John’s and Carolyn’s ashes were ceremoniously tossed into the Atlantic from a U.S. Navy ship, the USS Briscoe, off the Massachusetts coast near Martha’s Vineyard. Only close family attended the ceremony. John wasn’t in the Navy, he wasn’t a seaman, and he didn’t live in Massachusetts. Strange indeed there is no place to go and pay tribute to John.

John F. Kennedy Jr. had the potential to do great things. He embodied a unique convergence of factors: he was a good and smart person, endowed with the trust and goodwill—both inherited and earned—of most of the world. During his entire short life, he worked diligently to turn all that he’d been born with into something of value. I’d bet the ranch he would have become President, but there were other jobs and charity labor he could have done well, too. John mentioned that the United Nations had never had an American secretary-general. It’s a thought. I used to tell my wife that John would be there when his country needed him. John had a worldly and inclusive vision of America, a deep patriotism that was nonetheless open-hearted and sophisticated about the connectedness of the world’s nations. In this he was like his father, who in a speech not long after World War II spoke of the world’s need to “recognize how interdependent we are.” John had a marvelous pantheon of heroes, including Abraham Lincoln (John loved the quote “Am I not destroying my enemies when I make friends of them?”) When I think of John and his buddies, I see him in his favorite shirt, an old Racer X T-shirt. Racer X was the mysterious, long-lost brother of Speed Racer, the popular cartoon character of our youth. An orphan of sorts, Racer X wore a face mask to conceal his true identity. He was a top Formula One driver as well as a secret agent for the international police who would appear out of nowhere “to save his brother from dire circumstances,” according to the official Speed Racer history. Eventually Racer X stops racing to become a full-time secret agent. “No longer lured by fast cars, he turns his attention to the much more dangerous game of establishing world peace,” the story goes. Just before Racer X leaves racing for good, though, he vows to his unconscious brother (whom he’s just saved again) that he’ll “be near if you ever need help, no matter where you might go.” —John F. Kennedy Jr: America’s Reluctant Prince (2019) by Steven M. Gillon

John F. Kennedy Jr (George magazine, 1998): "Somehow I have been set up to be a great man. The thing is most of great men in history, my father included, could be shitheads as family men when they went home. I think it would be more interesting to be a good man than a great man. A bigger challenge for me would be to become a good man. And maybe not many people would know it, but I would have the satisfaction of knowing."